The Synthesis and Spectroscopy of a Self-Assembled
Catenane Monolayer
An Honors Thesis (Honrs 499)
By
Deborah L. Pinkstaff
Thesis Advisor
Dr. Patricia L. Lang
Ball State University
Muncie, Indiana
December 11, 1998
Expected Graduation: May 1999
-
A Brief Introduction
I received an undergraduate honors fellowship to do chemistry research
under Dr. Patricia Lang, the fall semester of my junior year. I started my
research, and have continued throughout both my junior and senior years here
at Ball State University. The basis of my research has been to synthesize and
characterize a self-assembled catenane monolayer.
The major goals of my research have been to synthesize both compounds
needed to assemble the catenane monolayer and to characterize them using
different types of spectroscopy. The types of spectroscopy I have been using
include NMR and IR spectroscopy.
The following presentation was given at the Indiana Academy of Science,
held on October 30, 1998. The topic of my presentation is the synthesis and
characterization of the Bis(thiol)hydroquinone Derivative. This is the first of two
compounds needed to form the catenane monolayer. I synthesized the
bis(thiol)hydroquinone derivative and characterized it using NMR and IR
spectroscopy.
-
Acknowledgments
I would like to thank the Ball State University Undergraduate Honors
Fellowship Program and the Ball State University Summer Research Grant for
my funding. I would also like to thank the Ball State University Chemistry
Department for the opportunity to participate in research.
I would like to thank Dr. Storhoff for all his help with my research.
appreciate all the ideas he gave us. I would also like to thank him for the use of
his equipment. I would also like to thank Dr. Kruger for his help with Chern
Windows, and in assigning our NMR peaks.
I would especially like to thank Dr. Patricia Lang for all of her help, guidance
and wisdom. I could not have asked for a better mentor. I enjoyed every aspect
of my research. It was a wonderful opportunity, and I am grateful for all of her
help. The beautiful aroma of thiol will always be with me.
Lastly, I would like to thank my family and friends for all their love and
support.
-
The Synthesis and Spectroscopy of a Self-Assembled Catenane
Monolayer
Introduction
A self-assembled monolayer, (SAM), refers to a single layer of organic
molecules adsorbed from solution to a metal surface. Self-assembled
monolayers have several applications. Some applications include: the study of
adhesion, biological interfaces, corrosion, electrochemistry organic surfaces and
wettability .
The majority of previous studies have focussed on SAMs of alkanethiols and
disulfides on gold surfaces. Less studied have been dithiols. A dithiol allows
the monolayer to attach to the gold surface in 2 places. This allows for more
control over orientation and conformational structure of the SAM. (See Figure 1)
Previous research was done by Gokel and his co-workers at University of
Miami. They synthesized the first surface attached catenane monolayer, and
studied it using cyclic voltametry and UVNIS spectroscopy. The aim of our
research is to study the IR spectroscopy of the same catenane monolayer on a
gold surface. A catenane monolayer is made up of two interlocking compounds,
like a bead and thread. The dithiol threads through the cyclophane and attaches
to the gold surface at both ends. Gokel's results are published in the J. Am.
Chern. Soc., 1993, 115,2542-2543. (See Figure 2)
--
We must first begin with the synthesis because the compounds cannot be
purchased.
Procedure
Step 1-Synthesis of the hydroquinone derivative.
The first step of our synthesis is to synthesize the hydroquinone derivative by
reacting hydroquinone with 2-{2-Chloroethoxy)ethanol. (See Figure 3)
Reference: Pedersen, C. J., J. Am. Chern. Soc., 1967,89, pg. 7017-7036
Figure 4 shows the 13C NMR spectrum of the hydroquinone derivative (diol).
The following assignments are made.
13C NMR Spectrum of Diol
I Corresponding Carbon on diol 2eak frequency (PPM) I
I F_arthest f~om ring_ -C-Q!!___ _ 161.7262
=:]
68.11 09
__~
___~~69.7702---------~
I -O-C-C-OH
I -C-O-C-C:O~
-
I -O-C-C-O-C-
------
I 2C C?n ring with no H
L 4C ~QJ:!!1~'Nith H
-.1
72 .7293 ___.__________ ~
.
115.686?___. _______~
J§~.1001
J
Figure 5 shows the H NMR spectrum of the hydroquinone derivative.
H NMR Spectrum of Diol
The important features seen on this spectrum are as follows:
4 triplets of equal intensity are seen. These represent the H on the 4 C on the
chains off the ring.
Figure 6 shows the infrared spectrum of the hydroquinone derivative. The
following assignments are made.
-
IR Spectrum of Diol
Step 2-Synthesis of the dichloride.
The second step of our synthesis is to synthesize the dichloride by reacting the
hydroquinone derivative with thionyl chloride. (See Figure 3)
Reference: Pedersen, C. J., J. Am. Chern. Soc., 1967,89, pg. 7017-7036
Figure 7 shows the 13C NMR spectrum of the dichloride. The following
assignments are made.
13C NMR Spectrum of Dichloride
! Corresponding Carbon _~n Di~!1lori~~_ I Peak Frequency _(P!ML-'
. Farthestfrom ri!!9_C-CJ______________
42.80~______________ .____ _
-&-C-CI ______.____.___._________________~8187 ~ ___.____.______ . _______ _
69.9766
-C-O-C-C-CI -_._-------------------------- ----------'"---------,------O-£-C-O-C
_____________
L1.59~_______________.__
_~_g_<?_f!Jj~Y!ith ~C?J::L_________________
1~~ 7171 ________ . __ _
_____--'-15~~t~36________
4C on ring with H.
J
Figure 8 shows the H NMR spectrum of the dichloride~
H NMR Spectrum on Dichloride
The proton spectrum is consistent with the Dichloride molecule as we".
-.
-
Figure 9 shows the infrared spectrum of the dichloride. The following
assignments are made.
IR Spectrum of Dichloride
~----------------~~------~~~-----------------
\ Pea~ FrequencYJc~~t Source of Peak
_________
i 3441.0
v(O-H) H-bonde<! stretch-residual'!VateL_
11645.0 ------------- Residual water
1----·--_··_-----_·_-_·__··_-------
---.--.--.---..-.---...- - .....
I~ §..~-~..:~ ------ -- -- -- -- --- --- _v(C-C) benzene ring stretch
___ .________
~l!~if - _- =--~-8g~gI:::~ :::~~=~~-~~-~-~31~-------------
I ~_out of plane bend-_.benzene
L~§_~:_~_______.__________.L_v(Q=_Cll stretch
. ---------1
_________._._____._____ .____..J
We see that the characteristic non-H-bonding stretch is no longer present. The
H-bonded stretch is due to residual water.
Step 3-Synthesis of Dithiol-2 steps:
Step 3a-Synthesis of Isothiuronium Salt.
The synthesis of the bis(thiol)hydroquinone derivative is the final step of our
procedure. This step is done in two parts. In the first half of this step, we
synthesize the isothiuronium salt by reacting the dichloride with thiourea. (See
Figure 10)
Reference: Rabjohn, Organic Synthesis Collective Volume IV, pg. 401-403
Figure 11 shows the 13C NMR spectrum of the isothiuronium salt. The following
assignments are made .
-
.
13C NMR Spectrum of Isothiuronium Salt
~. Correspo~~i_ng Car!l~~~_l!ls_~!~!!I!~nium _Sa 11_ I Peak F~qu~!,cy (P~!!'l_11
II --C-S-C=NH
32.2648 -----------------------~-O-Q-C-S-9=NH-------67.6751.... __________________
~-C-O-C-C-S-C=NH
_____________
69.82~? ______________________ _
~-=-O-C-C-Q-C-C-S-C=NH
70.J 678 _____________________
I 2C on ring ~th no H
______________ 115.6330 ____________
4C_Q!}!in~th !!________________ _______ 1§3.Q465 _________________
I -C-S-C=NH
_
J 72.460~_______________
Upon expansion, we see another set of three peaks that are consistent with the
-------- - - - - - - - -
L
presence of a compound that has 1 isothiuronium salt end, and 1 chloride end.
We also see a peak at 183.7772 due to residual thiourea.
Using Chem Windows, we were able to compare our peak assignments to the
predicted values. The blue values are our actual values, and the red values are
the predicted values. From this, we can see that our assignments are correct.
Figure 13 shows the infrared spectrum of the isothiuronium salt. The following
aSSignments are made.
--
IR Spectrum of Isothiuronium Salt
Peak Frequency (cm-) Source of peak
~
3040.0 ______- I v(N=Hl, v(N-H,) stretches I
1510.8
v(C-C) benzene stretch
~22~.0 ==~ =lV(G-Q) "aryl 0" stretch__ 11114.2 _
~C-O-C) ether stretch___ _
__
L!Q~~~_______
_v(G!:irQL~ther ~tre~
Step 3b-Synthesis of Dithiol.
The final step of our synthesis is to synthesize the bis(thiol)hydroquinone
derivative by reacting the isothiuronium salt with KOH. This produces the
potassium salt. H2S04 is then added to produce the bis(thiol)hydroquinone
derivative. (See Figure10)
Reference: Rabjohn, Organic Synthesis Collective Volume IV, pg. 401-403
Figure 14 shows the 13C NMR spectrum of the bis(thiol)hydroquinone derivative.
The following assignments are made.
13C NMR Spectrum of Bis(thiol)hydroguinone derivative
Again, if we expand the spectrum, we see another set of 3 peaks that are
consistent with the presence of a compound containing 1 thiol end and 1
chloride end.
--
Again, using Chern Windows, we were able to compare our observed peak
frequencies with those predicted. And again, our predictions were correct.
Mistake on overhead: blue 71 should be blue 73. (See Figure 15)
II
Corresponding Carbon ! Observed Peak
on Dithiol
I Frequency (PPM)
Predicted Peak
Frequency (PPM)
~-~~ -O-£-C-SH
-C-SH ---======-124.3891=-~==-==~I 68.1033
---_.------._-_.
I-C-O-C-C-SH
______ 69.6249 ____ -O-C-C-O-C-C-SH
I 73.1040
-73
74
-------~-----------
-+
26 ___
70
I
I
~_~~~==~-==~=~:==~I
__ _._"""_.-_._._._----..
---------------1
~l_~C
29_~n
ring with no H _1-115.?Of8--==~=-==---tff5--=~-~=~==~-=~====_j
on ring with H ___.-lJ_~_~:1_~!~ ________l1§!L____________________ J
Figure 16 shows the infrared spectrum of the bis(thiol)hydroquinone derivative.
The following assignments are made.
IR Spectrum of Bis(thiol)hvdroguinone Derivative
I Peak Frequency .(c:m-1) I Source of Peak
2564.0
_____
v(S-!:i) stretch
1508.0
I v(C-C) benzene stretch
I v(C-O) "aryl 0_"_st_re_tc_h____ ~
1236.6
1118.5
I v(C-Q.-Ctether stretch
1042___6_
v (9_1j 2-0 )_ether stretch
823.7
i 8 out of plane bend-benzene
------------+---:--=------------------1
667.1
_
I v(C-CIL~!fetch_
_ _______
_+
The intenSity of the C-CI stretch at 667.2 is greatly reduced.
Future Research
Our next step will be to purify the dithiol and run grazing angle reflectance
-
infrared spectroscopy of the dithiol on a gold surface. Grazing angle reflectance
infrared spectroscopy (GAR IR) involves the use of the Perkin Elmer 1760X
FTIR Spectrometer and a grazing angle reflectance accessory. In this system,
the IR beam is sent into the monolayer at a grazing angle. Radiation is
absorbed by the monolayer, reflected off the gold surface and then absorbed
again as the beam passes back through the monolayer.
We will then synthesize the cyclophane, form the monolayer on a piece of
gold, and gain GAR IR spectra of the catenane monolayer on a gold surface.
(See Figure 17)
-
Acknowledgements (See Figure 18)
We would like to thank:
The Indiana Academy of Science
Ball State University Department of Chemistry Summer Research Program
Ball State University Undergraduate Fellowship Program
Ball State University Summer Research Grant
Dr. Kruger-for his help with our NMR assignments using Chern. Windows
Dr. Storhoff.-for all of his help!!
I would especially like to thank Dr. Lang for her help and guidance throughout
my research.
-
References
Lu, Tianbao, Litao Zhang, George W. Gokel Angel E. Kaifer, "The First SurfaceAttached Catenane: Self-Assembly of a Two-Component Monolayer" J. Am.
Chern. Soc. 1993, 115,2542-2543
Pedersen, C. J., "Cyclic Polyethers and Their Complexes with Metal Salts" J.
Am. Chern. Soc. 1967,89,7017-7036
Pretch, Erno. Ardras Furst, Martin Badertscher, Renate Burgin, Morton Munk,
"C13 Shift: A Computer Program for the Prediction of 13C-NMR Spectra Based
on an Open Set of Additivity Rules" J. Chern. Inf. Conput. Sci. 1992,32,291295.
Rabjohn, "Ethanedithiol" Organic Synthesis Collective Volume IV, 401-403
-
)
)
Self-Assembled
Monolayers
Single layer of molecules adsorbed from
solution to metal
Model for: adhesion, membranes,
corrosion, etc
Alkanethiols on gold are well studied
Dithiols attach at 2 terminal ends
FIGURE I
)
)
Previous Research
I Gokel, G. W., et aI., 1. Am. Chem. Soc.
1993, 115, 2542-2543
I Observed 1st surface attached catenane
monolayer
FiGURE 2
HO-()-OH
)
CI~OH
+
Hydroquinone
2(2-Chloroethoxy)ethanol
NaOH/H 20
1-Butanol
I\I\~
HO
0
0
o
1 \ 1 \ ..
"===T_\ 0
0
+
OH
Hydroquinone derivative
(Diol)
c(
II
s
'CI
Thionyl chloride
benzene
pyridine
Hel
c,1\00-o-o~~,
Pedersen, C. J., ·Cyclic Polyethers and Their Complexes with Metal Salts" J.
Am. Chem. Soc. 1967, 89, 7017-7036
FIGURE 3
Dichloride
iT
I
(Millions)
i~
I!
i:,
o
100.0
L........
III
200.0
,
I
«
300.0
,
!
,
400.0
,
!
500.0
,
,
--~
153.1001
IX
!\..
~1
~
Ii '0
Ii e
i;
'I
I!~
~
~
'I :::
,5-
(:)
1::;l
~~
j
I! Vl
,! ()
I
il
IN
o
(:)
N
9J
~'
_I
~I,
~ ~I
cl
0,
115.6865
--
~~
9
~I,
I ' It
,I
o
,
I
0)
~I~
I
8
I
OJ
(:)
I
~
I
'<
!
.c
a.
I
a
o
c
I!
05'
_.0
\0
o
(:,
o ::s
~CD
a.
CD
...,
~.
.....
77.5312
77.2101
76.8889
~gl~
~
72.7293-J
----g J
69.7702
68.1109 -
~
j
j
61.7262
-~~
o ~
~
<'
CD
:)
0)
I
!
!
~
p
(Millions)
0
1.0
2.0
3.0
,I"
I!!' ,
4.0
5.0
I, " " !
6.0
I
,
8.0
7.0
I.,., I""
I
,
9.0
10.0
• I"., r
11.0
"I,
12.0
"
r
13.0 14.0
1 ' , 1
,
15.0
I, ,
16.0
17.0 IS.1
,!, 1
!,'"
-
t
co
0
I.
I
~
....
:;)
(::;-
,--
-~
• .0
~
......--
'1
t, ----•
GJ
=
...
.
... ...
,.0
LJ)
.....r-.
C
::0
III
)
~
~
=
~
. .......-
~
,,"""'u • ..--
l-
~,
~
:~
..-,.....-s.~
(Jl
0.52469
....
.C
.........---..
,.s_
'-'110-",
l\J
~
f
C
0.51982
n.4S00S
"
:1:--
or.. .,
0.49987
o)~
O-,~
--.
I
II
r
~
I
Jr
°l f
oS'-g
g!~I~~.'
CD
i
~.
] I
~=:
1~
,
! i
1I
i ~
_l
b....:
I
¢o
(\'.
.,,-:::. c--,
°)lfl
O)L:
° ""
:1:-..
----
)
)
62.6
II
HOI"\[\O-o-O'\'\H
Hydroquinone derivative
(Diol)
55'
IT
45
40
35
33.D
I
4000.0
3500
3000
2000.0
600.0
CM-1
FIGURE 6
,
I
I
I,
I
!
I
~~
~~
~
,:
f
~
(
(
-
L
....;F-
~
~
!
~IOS·l:1>
,
;
r
I
c:i
'"
~
j
0
¢
o
g
.,
(I)
"0
·c
0
1:
u
ii
ji
----------------------~.
is
--1>LSl"S9
~99L6·69
["000_ _
(
I
I
I,
~
9L6"·IL
S1>OS·9L
....../ 09ll"U
(
O-.........IL1>1>·U
ci
00
u
i
I
o
g
I
I!
i
1
- ~~
.
I
0
-18
~
~
f'
0
ci
'~
LL
f C1:
ILIL·~II
!
i-
i
"r
I
o
c=
~
-:!F=
~
!,
~r
I
i,
~
I
LL
o
....
~
g
ul
r'l~
r
-~
~l
-'
o
~
-,0'
=1
~j
U/
o.~
t=~i
c,;
.'
-
~
X,
"
0·009
I
O·OO~
,
,
j
,
,
,
t·
O·OOV
• ,
• I
O·OOE
, • I '
0·00l:
•
,
i
t
I
o
0·001
(SUO!lI!W)
~
..........~
[T
(Millions)
o
II
30.0
20.0
10.0
1
!:-.-
i
il~
I
I
1'0
~:~==~------------==~------~-------
I
ISen
1'0
'I)
Ul
0.50308
()
/.,
)~
~
-O·
II, :::;
i
:J:
:s
:1I:
"-'
:z:
o
O' LlI
Q
II
a:
\"'n
(I)
VI
o
Il
(j),
c
....-0
fIl'
eo:
o
~~b
,.--~
3.82S4~
U~~:~
3.81~ c=~_
4.0763'-.
)
4.0644~ ~
'----
9
o.4
'C<-,
V
';0
~
1
Yl
o
~j
4.a.c-----
'f <f
'jO
6;0
~
N
'jO
'"
l~.o
11.0 It"
l~.o l~.o
1{.0
l~.o 1~.0_ 1U
I
f
o
If
0) 0
==~=~""",~~....c::.
4.a7n--
1 <.--;:
w
F
7 jO
-c...
....."
~
..
w
---
\N
3..:5,......-
...,..-....-).IJcn---
3.~
f0
;::
,.6$"'---
17
. ~= '\
s
OJ
<==
-I.
i
)
')
CII\[\0-Q-O"'a"cl ---~JJ\'I0l'I".:;-.- - - - - - - -_ _ _ _---,
Dichloride
35'
Jr
30
25'
20
15'
i'
6.3,
I
4000.0
I
3500
2000.0
600.0
Df-!
..
FIGURE 9
.
~.
)
)
S
c,/\00-o-o~"c,
+
2
H2N
/
~~
Thiourea
NH2
Dichloride
A
HN
s~~-o-Ij
~ or-'b/\s
_.
pNH
HN
NH2
2 HCI
2
Isothiuronium salt
~H
KS~~-o-·
f ~ OI\~K
1\ 1\
HS
°
0
-0-\\ ./\
/
'\
d
~
1\
'0
+
4 NH3 + 2 K2C0 3 + 2 KCI + 2 H2 0
SH
Bis(thiol) hydroquinone derivative
+ K2 S0 4
Rabjohn, -Ethanedithiol- Organic; Synthesis Collective Volume IV,.401-403
FIGURE 10
(Billions)
r
}-"- -
!
0.1
J
;
0.2
0.3
0.4
0.5
0.6
0.7
0.8
0.9
183.7772
;X
I
00
p
o
~..
J'tl
~l-oo)
'~
I~'0
1,'"It
i
172.4606 - -
-.I"
P1
!~
0;
j
. ::
! ::
1.1
1.0
0)
j
- ,
~ 0
1:2
8":
,-
l"
0 j
,,
>-U; j1
.:
11.1
() 153.1230
153.0465
p
1
O~
-.
'1
:;>
t; ,
. 1
3
1
t:i ~
j
0-
o
115.6330
115.5641
:::T
c'
:J
l
::0
'l
-a
>-~j
=J
P
o ,.j
1
o
(J)
o
j
OJ
-
c'
N
I
()
(J)
o
I).)
;:;:
~ yen~
z
I
~1
~~
o
00
o
o
70.1678~
69.8237 7:'0
69.5790 /
67.6751
, j
8j
48.2916r:Jl'
48.0775
47.8634
47.6493 .
47,4352
-~ ~
p..,
0'
~
32.2648
-""
1
,
p j
-...-'
)
)
51
$
mm._ ••• ". n
13C.,_ _ _ _ _•___
...._ _ _ _ _ _ _
$
1
tn
n
•
fa
·NTl"1
Tl S
'
J .1" ,,_I'
k,oectr
_._ _ _ _ _ _ _ _ _ _ _ _ _
• _ _ _ _._ _ _ _ _ _ ........~
Ilredicting
' the s.pectra Chcll1ical shifts fronl
_
... _
tr~
....... "'*,.;
(~llenl\\lindo\NS
.....-'
• Erno Pretch, Andras Furst, Martin Badertscher,
Renate Burgin, and Morton Munk, "C13Shift: A
Computer Program for the Prediction of 13CNMR Spectra Based on an Open Set of Additivity
Rules" J. Chern. Inf. Conput. Sci. 1992, 32,
291-295.
~
24
FIGURE 12
S~164
NH2
)
)
...,.
HN
s~~-o-~ ol\{\s
A
pNH
NH2
2 Hel
HN
2
Isothiuronium salt
0.787'--r-------------~r----------------------------,
0.75
0.70
ESY
0.60
0.55'
o 531 I
• 4000.7 3800
.
~
3S00 34ho 32ho 30ho 28ho 2sho 24ho 22ho 200~. 019ho 1sho 17ho 1sho 1sho 14ho 13ho 1200 1100 1000 900 800 S~. 6
CM-1
FIGUI~E
13
r-j'-'
o
'I
~
II
~
"'" 153.1918
,,,, 153.1765
_
:! ••
i
100.0
.........t
200.0
L...........
300.0
t,
400.0
I
500.0
,
L..
W)
OJ
o ~
-;:::;:
=s-
0)
=s-
O
~i
J
1
wi
0,
(:)
i ...
!w
()
I,
I
;
Pl
g.
I
~
'&.,
i ••
I
i
VI 1
0-'
§
,
700.d
1
(:)
.
600.0
!
>-
1'~ ~0
'I
1
(Millions)
en·
ci"
.;:;:;
'<
Q.
a
.0
c
5'
0
::l
Tl
;>1
(J)
115.7018
115.6788
>-
Q.
(J)
:::::!,
-
0
(:)
-I
D
III
8
(:)
-I
~~
<
m
<'
(J)
)
.)
(f)
I
8
(:)
00
P
77.4471 ___0
77. 1260
76.8125
73.104071.3759 ___.....
7
69.6249~0
69.5867 ...--0
68.1033
~
o
53.5293-
~
o
ts
o
3l.9437 - " ,
,
j
O...J
24.3891_°
1
-~
)
_or
)
Wynn r'Nwxwn
turn,.
we
'mn
,""'*'*7
k,IIJ·f1bace
~
_______
~
___. ________________ ________
~.
~
sa
57
.,
_y"
'7
7'
'us
t
l\llod.ifier
____ ___________._______________
d
~
[)ithiols ad11ere to gold
<.-
=nm=.s
surf~lces
on both ends.
74
1)-
" S II
H-S 24 68
26
Bis(thiol) hydroquinone derivative
FIGURE 15
-
I
~
(
0
(
8
Q)
>
2
~
m
>
·c
Q)
-c '
Q)
c
0
c
'5
0
Ri
>-
(
(
g
M
.l::
.Q
.....
.l::
II)
iIi
0
~
U)
I
0
§...,.
-
~
W
cr:
~
C)
LL
C"
e
-c
0
1O
0
Ri
)
)
Next...
I Grazing Angle Reflectance Infrared
(GAR IR) Spectroscopy of dithiol on gold
I Synthesis of Cyclophane
I Form SAM on gold su rface
I GAR IR spectroscopy on monolayer
d radiation
FlrJllP~
17
)
)
Acknowledgements
'i;'~\':;;' ",,::.:y~'..,:,:,,~~,,;:" ''''''''1Il'~f..<~:~:~~'0i::;'~-;'
_
Indiana Academy of Science
Ball State University Department of Chemistry
Summer Research Program
Ball State University Undergraduate Fellowship
Program
Ball State University Summer Research Grant
Dr. Storhoff!!
Dr. Lang
FIGURE
18
--
Appendix
This appendix includes other spectral data obtained, but not used in the
presentation. Peak assignments can be found directly on the spectra.
Figure 19 shows the H NMR spectrum of the isothiuronium salt.
Figure 20 show the H NMR spectrum of the bis(thiol)hydroquinone derivative.
-
(Millions)
o
1><
..
;
~'C
!ID
,;:l
~(I)
!'C
1
>
'--
7.1620...:I
6.8982____(:)
6.8845----
j~
l~
i§
,:2
j
0
]
i··
Ii
II
~I
Di
1.0 2.0 3.0 4.0 5.0 6.0 7.0 8.0 9.0 10.0 11.0 12.0 13.0 14.0 15.0 16.0 17.0 18.0 19.0 20.0 21.0 22.0
9'J
O!
1
rI
b'
-
0.24875
I
J
o'i
j~
4.7568-
III
;
I
.d
0.26229
0.34578
52.60888m
_.
-I
0.10049
Z
~(-oo):
.n;JO'l
• .0
...
,.0
...
,A
SA
~ ~
1t
0):
"I
('-'
~
.......
!,
i
en
--....."-
~
1
j
i
i
1
•
I
c
~
I
I
I
c·
a
2.
c
0..-
3
Vv
(I)
Q)
)"
;::;:
~
~
l!
:
t
I
-
::T
..,....
11
0
0
~
0.._
(0
~I
IV
Z
yen
Z
I-
)~
-
r
(Millions)
o
..><
'0
~
7.2517-
(/I
'0
-.I
.,It
0
6.836~
~
6.824
6.813
~.
1.0
\
2.0
, .. 1
!
3.0
. , ••
4.0
I,
5.0
6.0
7.0
".""
8.0
,,,,,.
9.0
,,1.
-
10.0 11.0 12.0 13.0 14.0 IS.0 16.0 17.0 18.0 19.0 20.0
t,,,!,,
1
""
.. I
! . . . . ' •• , , ! !
\.
I.
~m
l
I
r
17.61SSSm 79.'~3m
II
S'
O·
:I
..
X
0-
0
T1
5.2826-
?>
0.IS894
~I-
4.0644::::::,.
4.0525 ii!;I"
3.7924~O
3.7814
3.6825~
3.6660...---3.6495
V7
€
0.46891
....Q
('
044164
0.44421
l..~
-:r
W)l
to>
0
2.774~
2.7327-.......:§
2.7162/2.6961
~
\,N
(Xl
V"JOT.
/(:,
0.26389
0'
O)~
::T
0
in'
~
::T
.:;;
'<
N
....0
0-
0
I
1.6135-........::
1.5933...---1.5723
';:;=>
0.12261
-
E.
:J
0
a-ct<
0
I
..ij~
CD
CD
:::!,
-
<S"
~IS'
:J
0-
~
~
.0
CD
):
CJ)
0.0546:==.:,
-0.0168
I
~~'!R~~~
)~
-
-
A Brief Reflection
This presentation was the first professional presentation I have ever given.
From the time I began preparing for my presentation, until October 30, 1998
when I gave my presentation, I experienced many things I did not expect.
As I began gathering all the information to use for my presentation, I felt very
nervous. I also felt very unprepared, with no idea what to expect. I knew very
little about the Indiana Academy of Science; what I did know, was based only on
the knowledge of other students.
I had given an informal presentation over the summer for the Chemistry
department. This is a requirement of the summer research program. That talk
helped me determine what kind of audience I would be addressing in October. It
also helped me narrow down the types of information to include in my
presentation.
Still feeling unprepared, I had a practice run with Dr. Lang the day before I
was to give my talk. She helped make corrections in the language I used as well
as other little errors I had made. Dr. Lang also explained to me what I could
expect at the Indiana Academy of Science. I felt much more prepared and
confident going into my presentation.
Overall, I believe that my presentation went very well. I was only asked a few
questions, however, the questions that were asked, I was able to answer easily.
I feel that my presentation was very informative to the audience. All of my peers
-
agreed that it went very well.
I believe that the decision to do research was a very important one. It was a
great experience to actually participate in research. It was an even better
experience to present my research at the Indiana Academy of Science. I am
very grateful for the opportunity, and I know it has been and will continue to be
very beneficial to my career in Chemistry.